Chemistry 231
1
Organic Chemistry 231
Dr. Steven M. Kennedy
Office Hours:
318 Caputo Hall
[email protected] D2L Course Website: https://millersville.desire2learn.com/
Mondays, Tuesdays, and Fridays 11:00 am to 1:00 pm Other meeting times available by email appointment only.
Lecture (CRN 7776): MWF 8:00 – 8:50 am in 102 Brossman Hall Lab Section B (CRN 12634): Wednesdays 2:00 – 4:50 pm in 331 Caputo Hall Lab Section A (CRN 7777): Thursdays 1:00 – 3:50 pm in 331 Caputo Hall Lab Section C (CRN 14640): Wednesdays 6:00 – 8:50 pm in 331 Caputo Hall with Dr. Anthony S. Drager
Course Description
This course is the first semester of a 2-‐course sequence in Organic Chemistry. Organic chemistry is a graphical, textual, and verbal scientific language, and an active field of study, research, and scholarship. Chemistry 231 is a non-‐ mathematical, logical, problem-‐solving course. It focuses on the structures, functional groups, nomenclature, properties, reactivity, reaction mechanisms, and the synthesis of fundamental classes of organic compounds. Most of the examples presented contain underling principles and concepts that are applied repeatedly throughout this course and in future organic chemistry, biochemistry, molecular biology, and other science courses. Some practical applications of organic chemistry to biological processes (neuroscience, metabolism, pharmacology, toxicology, etc.) and everyday life (medicine, materials, household products, food science, etc.) will be presented from the perspective of course learning objectives. Due to the nature of the science covered, this course requires oodles of drawing. Consequently, to obtain full credit, all correct answers on quizzes and exams must include both drawings and key words.
Course Organization
This is a blended lecture, laboratory, and online course in which new topics are first presented using a variety of formats including: assigned textbook readings, our D2L course website, the WileyPlus online homework system, in lecture, or in laboratory. Our scheduled class lecture periods will be used for a combination of introducing new topics, reviewing key concepts, and demonstrating the application of new content through problem solving examples. The first week of this course is a partial review of selected general chemistry concepts invaluable in your study of organic chemistry (Chapter 1). Then, organic structures, functional groups, and acid-‐base chemistry will be explored in the context of fundamental organic chemistry as we quickly move through Chapters 2 and 3. The remainder of the course is organized by functional groups, molecular structure, and chemical reaction mechanisms. This course is fast paced, continually builds on what is learned in the first month, and is cumulative by nature.
Course Learning Objectives Upon your successful completion of Chemistry 231, you will be able to… 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12.
Recognize, name, and represent (draw) organic compounds and organic functional groups Estimate the attractive forces within and between molecules Analyze structural and stereochemical conformations, configurations, and isomers Compare the stability of organic molecules based on energy considerations Describe relationships between molecular structure, chemical reactivity, and physical properties Understand how and why organic compounds react the way they do Apply your knowledge of acid and base reactions to analyze common organic reactions Predict products, starting materials, and/or reagents based on functional groups as sites of reactivity Propose and defend mechanisms of elementary reaction electron flow using curved-‐arrow notation Design simple multi-‐step synthesis of organic products by using the organic reactions that you learn Apply what was learned, and reason a solution for related problems Appreciate the ubiquitous and ever-‐present relevance of organic chemistry to the world around us
S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
2
Why Learn Organic Chemistry?
Organic chemicals are everywhere and make up over 95% of the more than 91 million (and counting) known chemical substances. Natural and synthetic organic chemicals are in the clothes, cars, foods, toys, pharmaceuticals, plastics, and most other consumer goods that we use every day. Volatile organic chemicals are present in the air we breathe. A foundation in organic chemistry fundamentals is necessary to understand the structure, properties, and reactivity of drugs, biochemicals, and environmental chemicals, which impact biological metabolism, nutrition, disease, health, physiology, neurology, growth, and development. An understanding of organic chemistry can help us make rational social and political decisions with regard to chemicals in our society.
Curious, have questions, or need help? Please stop by my office during office hours for assistance outside of class. Ask me questions during laboratory. Set up an appointment via email, if my office hours don’t fit your schedule. Email me your chemistry questions. Start a discussion on our D2L site. Form a study group. Get a tutor. Free tutoring (individual or group) is also available through Student Services. Call or stop by the tutoring office in Lyle Hall for additional information. http://www.millersville.edu/tutoringcenter/schedules/chemistry.php
Required and Recommended Materials
Required and recommended materials for the lecture and laboratory portions of this course are listed below. To deeply learn, as apposed to surface learning or strategically learning, the fundamentals of any scientific discipline will require both substantial time and monetary investments. While the required materials are a monetary investment, please understand that these materials have been carefully selected in an effort to minimize the amount of time that it will take you to deeply learn fundamentals of organic chemistry. Please also consider that that you will use most of the required materials for this course in both Chemistry 231 and Chemistry 232. The textbook is also a valuable reference when taking related courses such as Biochemistry, Molecular Biology, Genetics, and other related courses.
Required Lecture Materials 1. Daily online access to . . . • Wiley Plus Homework Site • Chemistry 231 D2L course website • Your Millersville email account 2. The Textbook, Study Guide, and WileyPLUS Bundle is available at the MU bookstore for $350.70. It includes the following three items…
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Textbook – Organic Chemistry, 2nd Edition by David R. Klein. i. Organic Chemistry, 2nd by David R. Klein Edition (Binder Ready Version) ii. ISBN: 978-‐1-‐118-‐45431-‐2 iii. 1344 pages iv. December 2013, ©2015
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Student Study Guide and Solutions Manual i. Student Study Guide and Solutions Manual to accompany Organic Chemistry 2nd Ed. (BRV) ii. ISBN : 978-‐1-‐118-‐70081-‐5 iii. 1056 pages iv. January 2014, ©2015 WileyPLUS access for Klein’s Organic Chemistry, 2nd Edition
• S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
3
Recommended Lecture Materials 3. Molecular Model Kit for Organic Chemistry: for optional use on quizzes and exams. •
1013A/Organic Chemistry Set for Student http://www.maruzen.info/hgs/catalog/product_info.php?products_id=616
4. Organic Chemistry as a Second Language: First Semester Topics, 3rd Edition, David R. Klein, John Wiley & Sons, 2012, ISBN 9781118203774. Used, e-‐text, and older editions also available.
Required Laboratory Materials 5. Weekly Laboratory Assignments: Handouts provided in lecture and posted on our Chemistry 231 D2L Course Website one week prior to each lab. 6. Molecular Model Kit for Organic Chemistry. ß You will need this to complete at least two of the labs. Most molecular model kits for organic chemistry will suffice. I recommend the following option, which can be found online… http://www.maruzen.info/hgs/catalog/product_info.php?products_id=616 7. A scientific calculator capable of exponential notation, square roots, and logarithmic functions 8. Organic Chemistry Student Lab Notebook by Hayden-‐McNeil publisher is available for purchase at the MU Bookstore for $17.00. ISBN: 9781930882461 http://www.hmpublishing.com/products/organic-‐chemistry-‐spiral-‐bound.html • • • • • • • •
• • •
Top page is perforated, allowing the instructor to collect the original instead of the duplicate Available in 100 pages of carbonless sets Fully laminated front and back covers Back cover folds over to prevent bleed through between sets Durable plasticoil spiral binding allows notebook to lay flat Cover contains most up-‐to-‐date Periodic Table Sequentially numbered pages Table of Contents for students to keep track of their labs "How to Keep a Laboratory Notebook" guidelines from Dartmouth "Laboratory Safety" guidelines for students Signature blocks for student and witness Dimensions: 8.5x11"
9. Safety Goggles or Glasses -‐ Over-‐The-‐Glass (OTG) means over prescription glasses. Examples from Google searches for safety glasses and goggles or OTG safety glasses: a. http://www.uline.com/Product/Detail/S-‐16223/Safety-‐Glasses-‐Goggles/Safety-‐Goggles-‐Indirect b. http://www.uline.com/Grp_208/Safety-‐Glasses-‐Goggles
10. One combination lock to share with your lab partner. S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
4
Lecture Schedule (MWF, 8:00 – 8:50 am, Brossman Hall 102) Section
Chapter #
Chapter Title
Exam Schedule
1 Review & Fundamentals
Chapter 1 Chapter 2 Chapter 3
A Review of General Chemistry Molecular Representations Acids & Bases
EXAM 1 – Friday, February 13
2 Structure, Properties & Mechanism
Chapter 4 Chapter 5 Chapter 6
Alkanes & Cycloalkanes Stereoisomers Reaction Mechanisms
3 Reactions
Chapter 7 Chapter 8 Chapter 9 Chapter 10
Substitution Reactions Alkenes & Elimination Reactions st Addition Reactions of Alkenes EXAM 3 – Friday, May 1 Alkynes th CUMULATIVE FINAL EXAM – Friday, May 8 , 2:45 pm – 4:45 pm
th
th
EXAM 2 – Friday, March 20
Chapters 15 & 16 (Spectroscopy) will be discussed in the laboratory.
Exam Dates: Exam 1 (2/13); Exam 2 (3/20); Exam 3 (5/1); Final Exam (5/8) Note: If a class is canceled due to adverse weather, then the missed exam will be given the next time the class meets. Check the Millersville University website for campus closure due to storms. http://millersville.edu/
Lecture Attendance, Exam & Quiz Policy You are responsible for all notes, discussions, assignments and handouts presented in each class (whether you are absent or present). You are expected to be present when any evaluation (quiz, test, etc.) is given. Absences that you know about in advance may be excused. Excused absences include attendance at university events (athletic and educational), military duty, bereavement, critical illness in the family, or personal illness in which a physician indicates that you were too ill to attend class. A request for an excused absence should include a written justification of the reason for the absence and be signed by the appropriate individual (coach, faculty member, physician, etc.). Only valid excuses will be accepted to make up any missed assignments. Work not made up will receive a grade of zero. Departure times for travel before university breaks are not a valid excuse to miss class, so please make your travel arrangements accordingly. Most exams are on Friday mornings. Please see the University Attendance Policy for more information. http://www.millersville.edu/registrar/faculty/attendance_policy.php
Classroom Etiquette
Feel free to ask questions in lecture; however, socializing and chatting off topic during class is rude and unfair to those students interested in learning and participating. If you persist in talking during class, you will be asked to leave. Please note that I reserve the right to take disruptive behavior such as habitual tardiness, frequent or excessive talking during class, cell phone disruptions, or leaving before class is over into account when determining your final grade.
Problem Solving
This is a non-‐mathematical problem-‐solving course. You must demonstrate that you can apply what you have learned to solve new problems. To pass this class with a respectable grade (C, B, or A) most students work problems every day of the semester. It is to your advantage that you work as many practice problems as it takes until a concept is mastered, even though most problems will not be collected or graded. There is a strong, direct correlation between the number of problems worked and understood to exam grades. There is an inverse correlation between the number of problems worked and understood to the perceived difficulty and length of exams. S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
5
Course Evaluation
7 Quizzes (7 x 20 points per quiz – 40 points = 100 points) 10.0 % Exam 1 (100 points) 10.0 % Exam 2 (125 points) 12.5 % Exam 3 (150 points) 15.0 % Cumulative Final Exam (200 pts.) 20.0 % Graded Online Homework Assignments (150 points) 15.0 % Laboratory (175 points) 17.5 % ∑ = 100.0 %
Final Course Grades
You MUST have at least a C-‐ average percentage grade (≥ 65.0 %) in the lecture portion of this course to count the laboratory grade Lecture portion 825 pts + Laboratory grade 175 pts Total points in course = 1000 pts
Grade Distribution (in percentage points) A
100 – 92.0
B
87.9 – 82.0
C
77.9 – 70.0 D
61.9 – 60.0
A-‐
91.9 – 90.0
B-‐
81.9 – 80.0
C-‐
69.9 – 65.0
D-‐
59.9 – 57.0
B+
89.9 – 88.0
C+
79.9 – 78.0
D+
64.9 – 62.0
F
< 57.0
Quizzes [7 x 20 points – 40 points = 100 points]
There will be seven (7) seven (7) minute pop quizzes (unscheduled quizzes). THERE ARE ABSOLUTELY NO MAKE-‐UP QUIZZES. Any quiz missed is a zero. Your two lowest quiz scores will be dropped from the D2L grade book after quiz number 7 is graded.
Hourly Exams [375 points] There will be three 50-‐minute exams given during the scheduled lecture time on the days indicated on the lecture schedule. Attendance at exams is mandatory. Exam 1 is worth 100 points, Exam 2 is worth 125 points, Exam 3 is worth 150 points.
Cumulative Final Exam [200 points] There will be one 120-‐minute cumulative final exam given during the scheduled final exam week time on the day indicated on the lecture schedule. Attendance at the final exam is mandatory. This fourth and final exam will be held only during the pre-‐arranged final exam period for this lecture time.
Graded Online Homework Assignments via WileyPlus [150 points] These points will be added to the grade book before the end of the semester based on your online assignment grades in WileyPlus. More information will be provided during the first week of class.
Laboratory [175 points] The open laboratory notebook lab final exam is worth 30 points. The spectroscopy problem sets are worth 45 points total. Pre-‐ laboratory assignments, proper laboratory notebook entries, and post-‐laboratory assignments are worth 100 points total.
Academic Honesty & Dishonesty
Plagiarism is the deliberate or even accidental representation of another’s work as your own without proper reference. Although you will work together on some material and experiments, this does not mean that lab reports and assignments should be identical. Each participant uses the collective data and discussion to prepare his or her own individual report. You should be familiar with the University policy on academic honesty and dishonesty as outlined in the Student Handbook and Academic Honesty and Dishonesty brochure; the content applies to this course. If you are caught, you will be removed from the course, assigned an F for the course, and a report will be filed with the associate Provost for Academic Programs and Services. S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
6
Tips for Success:
Solve as many problems as possible. Then solve more problems. Do not try to memorize every individual thing for this course. It will not work well. Instead, try to focus on the major concepts, and examples, and develop some flexibility in the application of those concepts to new examples. Look for similarities and difference in the course content. Make connections and organize new information based on your understanding of old information. While there are fundamental principles, concepts, structures, and vocabulary that must be remembered (memorized), successful completion of this course depends upon your ability to problem solve by utilizing newly acquired information. • Be curious. • Do good work. • Problems are puzzles. • Work lots of problems. • Then do more problems! • Learn to enjoy problem solving. • Make the problem solving a game. • When in doubt, draw it out. Practice drawing structures. • Actively attend lecture. And, take good notes to practice quickly drawing correct structures. • Don’t get behind in this class due to the pace of this course. This is not the type of class that you can effectively cram for. • If you do happen to cram your way through this course by using surface learning strategies, then how will you ever pass Chemistry 232 next semester after forgetting fundamentals that you did not commit to long-‐term memory? • Do all of the required readings before each lecture. Each chapter covered is required reading. Own the fact that you are responsible for all material in each chapter of the textbook, even if we do not cover it in lecture. • Devote time to this class! You are not given a grade; you earn your grade. You cannot realistically expect to learn even the basics of a subject by spending the typical 1 to 2 hours a week that many students report putting into some courses. • A rule-‐of thumb in study time for this course should be at least 4 hours for each 1 hour spent in class per week. • To obtain a passing “C” letter grade, I recommend at least 12 hours of study time outside of class per week. • Ask questions! There is no such thing as a “dumb” question. Get help when needed!!! Don’t put it off. • Put in the time and work hard. • Above all, have fun with it! S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
7
Learning Accommodations Please see the Office of Learning Services in Lyle Hall (http://www.millersville.edu/learningservices/) as soon as possible if you have special learning needs for this class. If you have a condition that may affect your ability to perform laboratory exercises, to exit lab safely from the premises in an emergency, or which may cause an emergency during class, or lab, please discuss this in confidence with your instructor and someone at the Office of Student Support Services. Appropriate accommodations may then be provided.
Laboratory Objectives
At the completion of CHEM 231 Laboratory, you should be able to… 1. Demonstrate proper laboratory safety when working in the lab 2. Keep a neat and organized record of laboratory data in a notebook 3. Demonstrate proper methods to categorize and dispose of chemical waste 4. Set up apparatus for experimental techniques: reactions, distillations, filtrations, etc. 5. Purify organic products by recrystallization (solids) and distillation (liquids) 6. Characterize organic products by physical, chemical, and spectroscopic properties 7. Solve unknown organic structures using 1D NMR spectral data 8. Explain any of the experiments that we conducted using key words and drawings
Laboratory Schedule* Week 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Week of st
Jan 21 Jan 28th Feb 4th Feb 11th Feb 18th Feb 25th Mar 4th Mar 11th Mar 18th Mar 25th Apr 1st Apr 8th Apr 15th Apr 22nd Apr 29th
EXPERIMENT Check-‐in // Safety // IUPAC Naming // Structures // Physical Constants // MSDS IR Spectroscopy of Functional Groups Recrystallization Goody’s Powder (Acid-‐Base Extraction) Analgesics & Thin Layer Chromatography (TLC) Conformations of Alkanes: Molecular Models Part 1 Stereoisomerism: Molecular Models Part 2 // Notebooks Collected in Lab Spring Break Introduction to Proton & Carbon NMR – Spectroscopy PS1 Nucleophilic Substitution of Alkyl Halides Alcohol Elimination: Preparation of an Alkene More Proton and Carbon NMR – Spectroscopy PS2 Extracting Limonene from Oranges (Distillation) Synthesis of Aspirin Open Notebook & Spectroscopy Exam // Notebooks Collected in Lab // Check-‐out
*Note: experiments subject to change.
Lab Attendance: Attendance at each laboratory session is mandatory. Failure to attend each and every laboratory meeting equals failure of this course. Only valid excuses will be accepted in order to make up labs. In the event of an anticipated excused absence, arrangements should be made to make up work prior to the absence. Students are not allowed to work by themselves when there is not a lab in session. You are expected to have read the procedure thoroughly, to have prepared your notebook based on the notebook guidelines for this course, and to have completed the weekly pre-‐laboratory assignment prior to each lab. SAFETY IS VERY IMPORTANT IN THE LABORATORY. General safety guidelines will be presented in the laboratory and should be followed at all times. Specific safety precautions for each experiment will be covered before each lab. Failure to follow safety guidelines is reason for dismissal from a lab and a grade of zero on the experiment. Additional laboratory guidelines including notebooks and reports are covered in the week 1 handouts. S. M. Kennedy
Spring Semester 2015
Updated 1/15/2015
Chemistry 231
8
Contract for a Course Evaluation Scheme Due On: Friday, February 20th @ 8:50 am (at the end of Lecture) Name (Last, First) ____________________________________________________________
By writing your initials in the box below, you choose to follow the Course Evaluation Scheme Selected. Course Evaluation Options:
Original Course Evaluation Scheme 7 Quizzes (7 x 20 points per quiz – 40 points = 100 points) 10.0 % I will follow the Exam 1 (100 points) 10.0 % 12.5 % original syllabus Exam 2 (125 points) Exam 3 (150 points) 15.0 % for this course & Cumulative Final Exam (200 pts.) 20.0 % use Wiley Plus to Graded Online Homework Assignments (150 points) 15.0 % 17.5 % obtain homework Laboratory (175 points) ∑ = 100.0 % points. Final Course Grades You MUST have at least a C-‐ average percentage grade (≥ 65.0 %) in the lecture portion of
this course to count the laboratory grade Lecture portion 825 pts + Laboratory grade 175 pts Total points in course = 1000 pts
No Wiley Plus Homework Course Evaluation Scheme I choose to forfeit 7 Quizzes (7 x 20 points per quiz – 40 points = 100 points) 11.8 % Exam 1 (100 points) 11.8 % all possible Exam 2 (125 points) 14.7 % points for doing Exam 3 (150 points) 17.6 % 23.5 % homework. Do Cumulative Final Exam (200 pts.) Laboratory ( 175 p oints) 20.6 % not include any ∑ = 100.0 % homework points Final Course Grades in my grade. You MUST have at least a C-‐ average percentage grade (≥ 65.0 %) in the lecture portion of this course to count the laboratory grade
Lecture portion 675 pts + Laboratory grade 175 pts Total points in course = 850 pts
Your choice is final; your choice will not be reversed after the due date of Friday, February 20th at 8:50 am. Handing in this signed contract, with your choice is worth 2 extra credit points. If you do not hand in a signed contract, then you automatically choose the Original Course Evaluation Scheme as outlined in the original Syllabus for this course.
Signature ______________________________________ S. M. Kennedy
Spring Semester 2015
Date ____________ Updated 1/15/2015
